%0 Journal Article %A Gonzalez-de-Castro, Angela %A Xiao, Jianliang %D 2015 %T Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2 %U https://acs.figshare.com/articles/journal_contribution/Green_and_Efficient_Iron_Catalyzed_Selective_Oxidation_of_Olefins_to_Carbonyls_with_O_sub_2_sub_/2154343 %R 10.1021/jacs.5b03956.s001 %2 https://acs.figshare.com/ndownloader/files/3788194 %K Efficient %K formation %K chemoselectivity %K Olefin %K species %K pyridine bisimidazoline ligand %K olefins %K Oxidation %K Catalyzed %K mechanism %K Fe %K iron center %K 1 atm %K benzaldehyde %K carbonyl product %K oxidation %K Various observations %K olefinic substrate %K carbonyl compounds %K halo %K halide migration %K group tolerance %K Carbonyl %K yield %K ketone %K acetophenone %K styrene %K O 2A %K dioxetane %X A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe­(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. %I ACS Publications